Direct Metal- and Reagent-Free Sulfonylation of Phenols with Sodium Sulfinates by Electrosynthesis.

A novel electrochemical strategy for the synthesis of aryl sulfones by direct sulfonylation of phenols with sodium sulfinates has been developed. The C,S-coupling products are of particular interest for chemical synthesis, material sciences and pharmaceutical sciences. By using this metal- and reagent-free electrochemical method, aryl and diaryl sulfones can be obtained directly in good yields. The established one-step protocol is easy to perform, scalable, inherently safe, and enables a broad scope, which is not limited by quinoid-forming substrates.

• Publication year

  2019

• Venue

  Chemistry

• Publication date

  2019-04-08

• Fields of study

  Medicine, Materials Science, Chemistry

• Identifiers
  DOI 10.1002/chem.201900850PMID 30861196
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Use of Boron‐Doped Diamond Electrodes in Electro‐Organic Synthesis

  2019cited by this paper
• Electrochemical Coupling of Benzothiophenes with Phenols

  2018cited by this paper
• Electrochemical Arylation Reaction.

  2018cited by this paper
• Modern Electrochemical Aspects for the Synthesis of Value‐Added Organic Products

  2018cited by this paper
• Cross‐Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis

  2018cited by this paper
• Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis.

  2018cited by this paper
• Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides.

  2018cited by this paper
• Regioselective Metal- and Reagent-Free Arylation of Benzothiophenes by Dehydrogenative Electrosynthesis.

  2018cited by this paper
• Regioselektive metall‐ und reagenzfreie Arylierung von Benzothiophenen durch dehydrierende Elektrosynthese

  2018cited by this paper
• Solvent Control in Electro-Organic Synthesis

  2018cited by this paper
• Metal‐ and Reagent‐Free Anodic Dehydrogenative Cross‐Coupling of Naphthylamines with Phenols

  2018cited by this paper
• Visible-Light-Driven Silver-Catalyzed One-Pot Approach: A Selective Synthesis of Diaryl Sulfoxides and Diaryl Sulfones.

  2018cited by this paper
• Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl-Containing Molecules.

  2018cited by this paper
• Electrifying Organic Synthesis

  2018cited by this paper
• Reagent- and Metal-Free Anodic C-C Cross-Coupling of Aniline Derivatives.

  2017cited by this paper
• Hexafluoroisopropanol as a highly versatile solvent

  2017cited by this paper
• Reagens‐ und metallfreie anodische C‐C‐Kreuzkupplung von Anilinderivaten

  2017cited by this paper
• Einfache und doppelte metall‐ und reagensfreie anodische C‐C‐Kreuzkupplung von Phenolen mit Thiophenen

  2017cited by this paper
• Electrooxidative Metal‐Free Dehydrogenative α‐Sulfonylation of 1H‐Indole with Sodium Sulfinates

  2017cited by this paper
• The Catalytic Effect of Fluoroalcohol Mixtures Depends on Domain Formation

  2017cited by this paper
• Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes.

  2017cited by this paper
• Electro-organic Synthesis as a Sustainable Alternative for Dehydrogenative Cross-Coupling of Phenols and Naphthols

  2016cited by this paper
• Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent- and Metal-Free Anodic Cross-Coupling Reaction.

  2016cited by this paper
• Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry.

  2016cited by this paper
• Synthesis of meta-Terphenyl-2,2''-diols by Anodic C-C Cross-Coupling Reactions.

  2016cited by this paper
• Synthese von meta‐Terphenyl‐2,2′′‐diolen durch anodische C‐C‐Kreuzkupplungen

  2016cited by this paper
• New route for the synthesis of N-alkyl-2-(phenylsulfonyl)anilines

  2016cited by this paper
• Selektive Synthese teilgeschützter unsymmetrischer Biphenole durch reagens‐ und metallfreie anodische Kreuzkupplung

  2016cited by this paper
• Electrochemical Screening for Electroorganic Synthesis

  2016cited by this paper
• Product diversity by changing the electrode potential. Synthesis, kinetic evaluation and antibacterial activity of arylsulfonyl-4,4'-biphenol and bis-arylsulfonyl-4,4'-biphenol derivatives

  2016cited by this paper
• An Efficient Electrochemical Synthesis of Vinyl Sulfones from Sodium Sulfinates and Olefins.

  2015cited by this paper
• Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol.

  2015cited by this paper
• Cover Picture: Metal‐ and Reagent‐Free Highly Selective Anodic Cross‐Coupling Reaction of Phenols (Angew. Chem. Int. Ed. 20/2014)

  2014cited by this paper
• Copper-catalysed Coupling of Aryl Tosylates with Sodium Arylsulfinates

  2014cited by this paper
• Desulfurization of thianthrene by a Gordonia sp. IITR100

  2014cited by this paper
• Metall‐ und reagensfreie hochselektive anodische Kreuzkupplung von Phenolen

  2014cited by this paper
• Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts.

  2013cited by this paper
• Arylation of lithium sulfinates with diaryliodonium salts: a direct and versatile access to arylsulfones.

  2013cited by this paper
• Modeling analysis of electrode fouling during electrolysis of phenolic compounds

  2013cited by this paper
• Efficient Factors on the Reaction Rate and Site-Selectivity in Sulfonylation of Catechol and Hydroquinone Derivatives: Experimental and Theoretical Studies

  2013cited by this paper
• Multilayered sulphonated polysulfone/silica composite membranes for fuel cell applications

  2012cited by this paper
• Oral hedgehog-pathway inhibitors for basal-cell carcinoma.

  2012cited by this paper
• Efficient anodic and direct phenol-arene C,C cross-coupling: the benign role of water or methanol.

  2012cited by this paper
• Boron-doped diamond electrodes for electroorganic chemistry.

  2012cited by this paper
• A green approach for the electrochemical synthesis of 4-morpholino-2-(arylsulfonyl)benzenamines

  2010cited by this paper
• Organic electrosynthesis: a promising green methodology in organic chemistry

  2010cited by this paper
• Anodische Phenol‐Aren‐Kreuzkupplung an bordotierten Diamantelektroden

  2010cited by this paper
• Polystyrene Supported Al(OTf)3: a Stable, Efficient, Selective, and Reusable Catalyst for Sulfonylation of Arenes with Sulfonic Acids

  2010cited by this paper
• Anodic phenol-arene cross-coupling reaction on boron-doped diamond electrodes.

  2010cited by this paper
• Paired electrochemical synthesis of new organosulfone derivatives

  2008cited by this paper
• Polystyrene and silica gel supported AlCl3 as highly chemoselective heterogeneous Lewis acid catalysts for Friedel–Crafts sulfonylation of aromatic compounds

  2007cited by this paper
• Vinyl sulfones: Synthetic preparations and medicinal chemistry applications

  2006cited by this paper
• Diaryl Sulfones Through Oxidative Coupling of Catechols and Arylsulfinic Acids

  2006cited by this paper
• Graphite/Methanesulfonic Acid (GMA) as a New Reagent for Sulfonylation of Phenols and Thia-Fries Rearrangement of Aryl Sulfonates to Sulfonylphenols

  2005cited by this paper
• Direct Sulfonylation of Aromatic Rings with Aryl or Alkyl Sulfonic Acid Using Supported P2O5/Al2O3

  2005cited by this paper
• Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides.

  2004cited by this paper
• Bicalutamide

  2004cited by this paper
• Electrochemical oxidation of quercetin in the presence of benzenesulfinic acids

  2003cited by this paper
• An Efficient Method for the Sulfonylation of Aromatic Rings with Arene/Alkane Sulfonic Acid by Using P2O5/SiO2 under Heterogeneous Conditions §

  2003cited by this paper
• The cathodic behaviour of poly(alkyl) and (aryl) sulfones revisited. Mechanistic and theoretical approaches

  2003cited by this paper
• Electro-oxidation of catechols in the presence of benzenesulfinic acid. Application to electro-organic synthesis of new sulfone derivatives

  2002cited by this paper
• Oxidation of 4-chlorophenol at boron-doped diamond electrode for wastewater treatment

  2001cited by this paper
• Electrochemical oxidation of phenol at boron-doped diamond electrode. Application to electro-organic synthesis and wastewater treatment.

  2001cited by this paper
• Acylation and related reactions under microwaves. 4. Sulfonylation reactions of aromatics.

  2001cited by this paper
• Indium-Catalysed Aryl and Alkyl Sulfonylation of Aromatics

  2001cited by this paper
• CATHODIC BEHAVIOUR OF 1-CYCLOALKEN-1-YL PHENYL SULFONES. I. COMPETITION AMONG DIMERIZATION, CLEAVAGE, ISOMERIZATION AND OLIGOMERIZATION PROCESSES IN A PROTIC MEDIA

  1999cited by this paper
• Bismuth(III) Trifluoromethanesulfonate: An Efficient Catalyst for the Sulfonylation of Arenes

  1999cited by this paper
• 2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones.

  1996cited by this paper
• 1,1,1,3,3,3-Hexafluoropropan-2-ol as a solvent for the generation of highly persistent radical cations

  1995cited by this paper
• A recent survey on the cathodic behaviour of sulfones : is cleavage the unavoidable fate ?

  1993cited by this paper
• 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.

  1993cited by this paper
• Cathodic cleavage of heteroarylalkylsulfones : A facile route to long chain aliphatic sulfinates and relevant sulfones.

  1992cited by this paper
• Dapsone *

  1979cited by this paper
• Ueber eine neue Synthese aromatischer Sulfone

  year unknowncited by this paper

• Substrate-controlled regioselective C(sp2)-H sulfonylation of ortho-aminophenols.

  2025cites this paper
• Dual Roles of Supporting Electrolytes in Organic Electrosynthesis

  2024cites this paper
• Recent Advances of C−S Coupling Reaction of (Hetero)Arenes by C−H Functionalization

  2024cites this paper
• Electrochemical Trifluoromethylation of Enamides under Microflow Conditions

  2024cites this paper
• Catalyst-Free Electrochemical Sulfonylation of Organoboronic Acids.

  2023cites this paper
• Supporting Electrolyte-Free Electrochemical Oxidative C-H Sulfonylation and Thiocyanation of Fused Pyrimidin-4-ones in an All-Green Electrolytic System.

  2023cites this paper
• Research Progress of Electrochemical Synthesis of C-Sulfonyl Compounds

  2023cites this paper
• Electrochemical Regioselective Sulfenylation of 2H-Indazoles with Thiols in Batch and Continuous Flow.

  2022cites this paper
• Regio- and stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

  2021cites this paper
• Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation

  2021cites this paper
• Practical Electro-Oxidative Sulfonylation of Phenols with Sodium Arenesulfinates Generating Arylsulfonate Esters.

  2021cites this paper
• Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

  2021cites this paper
• An electrolyte- and catalyst-free electrooxidative sulfonylation of imidazo[1,2-a]pyridines

  2021cites this paper
• Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines.

  2021cites this paper
• Electrochemical‐In‐Situ‐Oxidative Sulfonylation of Phenols with Sulfinic Acids as an Access to Sulfonylated Hydroquinones

  2021cites this paper
• Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones

  2021cites this paper
• Mn(OAc) 3 ‐Mediated Sulfonylation of Vinyl Azides Resulting in N ‐Unsubstituted Enaminosulfones

  2021cites this paper
• Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.

  2021cites this paper
• Enhanced degradation of phenol by a novel biomaterial through the immobilization of bacteria on cationic straw.

  2021cites this paper
• Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis

  2021cites this paper
• Sulfenylation of Indoles Mediated by Iodine and Its Compounds

  2021cites this paper
• Review—Use of 1,1,1,3,3,3–hexafluoro–2–propanol (HFIP) Co-Solvent Mixtures in Organic Electrosynthesis

  2020cites this paper
• Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

  2020cites this paper
• Introducing a New Michael Type Acceptor: A Green Strategy for the Synthesis of Organic Compounds

  2020cites this paper
• Electrosynthesis 2.0 in 1,1,1,3,3,3‐Hexafluoroisopropanol/Amine Mixtures

  2020cites this paper
• Regioselective C-H Sulfonylation of 2H-Indazoles by Electrosynthesis.

  2020cites this paper
• Removal of phenol from aqueous solution using acid-modified Pseudomonas putida-sepiolite/ZIF-8 bio-nanocomposites.

  2020cites this paper
• Metal‐ and Reagent‐Free Electrochemical Synthesis of Alkyl Arylsulfonates in a Multi‐Component Reaction

  2020cites this paper
• Chemistry of electrochemical oxidative reactions of sulfinate salts

  2020cites this paper
• Electrochemical Radical-Radical Cross-Coupling Approach between Sodium Sulfinates and 2H-Indazoles to 3-Sulfonylated 2H-Indazoles.

  2020cites this paper
• Electrochemical Oxidative C−H Sulfonylation of Anilines

  2019cites this paper
• Recent Advances in Electrochemical Chalcogen (S/Se)‐Functionalization of Organic Molecules

  2019cites this paper
• Electro-catalytic oxidative transformation of organic acids for carbon-heteroatom and sulfur-heteroatom bond formation.

  2019cites this paper
• Synthesis of Isoxazolines and Oxazines by Electrochemical Intermolecular [2 + 1 + n] Annulation: Diazo Compounds Act as Radical Acceptors.

  2019cites this paper
• Exogenous-oxidant- and catalyst-free electrochemical deoxygenative C2 sulfonylation of quinoline N-oxides.

  2019cites this paper
• Recent advances in C–S bond construction to synthesize sulfone

  2019cites this paper
• Transition-metal- and oxidant-free directed anodic C-H sulfonylation of N,N-disubstituted anilines with sulfinates.

  2019cites this paper
• Straightforward Electrochemical Sulfonylation of Arenes and Aniline Derivatives using Sodium Sulfinates

  2019cites this paper